NOVEL 26-OXYGENATED PRODUCTS IN MICROBIAL-DEGRADATION OF ERGOSTEROL

被引:7
作者
AMBRUS, G [1 ]
JEKKEL, A [1 ]
ILKOY, E [1 ]
HORVATH, G [1 ]
BOCSKEI, Z [1 ]
机构
[1] CHINOIN PHARMACEUT,BUDAPEST,HUNGARY
关键词
EGOSTEROL; MECHANISM OF MICROBIAL 26-OXIDATION;
D O I
10.1016/0039-128X(95)00078-5
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
In order to investigate the effect of the different stereochemistry of C-24 on the microbial C-26 oxidation of sterol side-chain the genetically modified Mycobacterium sp. BCS 396 strain was used to transform ergosterol. Ergosterol was converted to 3-oxo-4,22-ergostadien-26-oic acid methyl ester, 3-oxo-1,4,22-ergostatrien-26-oic acid methyl ester, and 3-oxo-1,4,22-ergostatrien-26-oic acid, the structures of which have been determined by IR, H-1 NMR, C-13 NMR, and mass spectroscopy. The X-ray structure of 3-oxo-4,22-ergostadien-26-oic acid methyl ester revealed that oxidation at C-26 of the ergostane side-chain generates a chiral center with S-configuration at C-25 as a result of chiral induction of the C-24 center.
引用
收藏
页码:626 / 629
页数:4
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